NPASS Compound

Structure

NPC474388 OpenBabel07101718242D 33 35 0 0 0 0 0 0 0 0999 V2000 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 19 2 0 0 0 0 11 24 2 0 0 0 0 11 30 1 0 0 0 0 12 25 2 0 0 0 0 12 31 1 0 0 0 0 13 26 2 0 0 0 0 13 32 1 0 0 0 0 14 22 1 0 0 0 0 15 28 1 0 0 0 0 16 17 2 0 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 18 20 2 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 33 1 0 0 0 0 20 21 1 0 0 0 0 21 23 1 0 0 0 0 21 27 2 0 0 0 0 22 23 2 0 0 0 0 22 33 1 0 0 0 0 23 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.11
Volume:	439.596
LogP:	2.728
LogD:	2.23
LogS:	-4.497
# Rotatable Bonds:	9
TPSA:	127.57
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.403
Synthetic Accessibility Score:	2.579
Fsp3:	0.217
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.831
MDCK Permeability:	3.672948514577001e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.223
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.328
Plasma Protein Binding (PPB):	78.15961456298828%
Volume Distribution (VD):	0.631
Pgp-substrate:	25.41499137878418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.615
CYP1A2-substrate:	0.17
CYP2C19-inhibitor:	0.78
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.855
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.517
CYP3A4-inhibitor:	0.601
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	2.183
Half-life (T1/2):	0.819

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.002
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.117
Rat Oral Acute Toxicity:	0.734
Maximum Recommended Daily Dose:	0.099
Skin Sensitization:	0.911
Carcinogencity:	0.045
Eye Corrosion:	0.006
Eye Irritation:	0.265
Respiratory Toxicity:	0.103

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC474388

Natural Product ID:	NPC474388
*Common Name:**	Rhamnazin Triacetate
IUPAC Name:	[4-(3,5-diacetyloxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl] acetate
Synonyms:	Rhamnazin Triacetate
Standard InCHIKey:	LODXNGWSMYYFFA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H20O10/c1-11(24)30-16-7-6-14(8-17(16)29-5)22-23(32-13(3)26)21(27)20-18(31-12(2)25)9-15(28-4)10-19(20)33-22/h6-10H,1-5H3
SMILES:	COc1cc(OC(=O)C)c2c(c1)oc(c(c2=O)OC(=O)C)c1ccc(c(c1)OC)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465819
PubChem CID:	44584491
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33118	Rhamnus	Genus	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350094]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
CELL-LINE	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	10.0	%	PMID[510271]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	14.3	%	PMID[510271]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	84.5	%	PMID[510271]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC474388 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	476
0.1-0.2	1904
0.2-0.3	4915
0.3-0.4	10535
0.4-0.5	7112
0.5-0.6	3939
0.6-0.7	5687
0.7-0.8	4738
0.8-0.85	2341
0.85-0.9	884
0.9-0.95	148
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472535
1.0	High Similarity	NPC474170
0.9931	High Similarity	NPC177839
0.9796	High Similarity	NPC122623
0.9796	High Similarity	NPC241774
0.9796	High Similarity	NPC34725
0.9796	High Similarity	NPC276059
0.973	High Similarity	NPC257277
0.9662	High Similarity	NPC471746
0.9653	High Similarity	NPC310259
0.9586	High Similarity	NPC299923
0.9524	High Similarity	NPC259058
0.9524	High Similarity	NPC201547
0.9456	High Similarity	NPC181250
0.9456	High Similarity	NPC69752
0.9444	High Similarity	NPC70853
0.9444	High Similarity	NPC9966
0.9388	High Similarity	NPC261548
0.9379	High Similarity	NPC113089
0.9375	High Similarity	NPC29536
0.9333	High Similarity	NPC186507
0.9329	High Similarity	NPC76376
0.9329	High Similarity	NPC236769
0.9324	High Similarity	NPC474648
0.932	High Similarity	NPC117463
0.932	High Similarity	NPC85233
0.9315	High Similarity	NPC136278
0.9306	High Similarity	NPC474037
0.929	High Similarity	NPC280893
0.9272	High Similarity	NPC284353
0.9267	High Similarity	NPC134677
0.9262	High Similarity	NPC166753
0.9262	High Similarity	NPC219330
0.9262	High Similarity	NPC50728
0.9257	High Similarity	NPC183236
0.9252	High Similarity	NPC106461
0.9252	High Similarity	NPC283002
0.9252	High Similarity	NPC14958
0.9252	High Similarity	NPC110639
0.9252	High Similarity	NPC40818
0.9252	High Similarity	NPC302408
0.9252	High Similarity	NPC215932
0.9231	High Similarity	NPC475214
0.9216	High Similarity	NPC257914
0.9216	High Similarity	NPC104459
0.9216	High Similarity	NPC238405
0.9211	High Similarity	NPC474983
0.9211	High Similarity	NPC178854
0.9205	High Similarity	NPC279930
0.9205	High Similarity	NPC58382
0.9205	High Similarity	NPC246204
0.9205	High Similarity	NPC78326
0.9205	High Similarity	NPC179126
0.9205	High Similarity	NPC236223
0.9205	High Similarity	NPC270620
0.9205	High Similarity	NPC162351
0.92	High Similarity	NPC474663
0.92	High Similarity	NPC198615
0.9195	High Similarity	NPC159103
0.9189	High Similarity	NPC205522
0.9184	High Similarity	NPC471590
0.9184	High Similarity	NPC165512
0.9161	High Similarity	NPC471745
0.9156	High Similarity	NPC477164
0.9145	High Similarity	NPC189960
0.9145	High Similarity	NPC32557
0.9139	High Similarity	NPC123886
0.9139	High Similarity	NPC279989
0.9139	High Similarity	NPC82325
0.9133	High Similarity	NPC29056
0.9128	High Similarity	NPC195202
0.9116	High Similarity	NPC23955
0.9116	High Similarity	NPC293201
0.9114	High Similarity	NPC476180
0.9114	High Similarity	NPC280493
0.9097	High Similarity	NPC112418
0.9091	High Similarity	NPC130894
0.9091	High Similarity	NPC25495
0.9091	High Similarity	NPC300943
0.9091	High Similarity	NPC176300
0.9091	High Similarity	NPC253634
0.9091	High Similarity	NPC4481
0.9091	High Similarity	NPC105242
0.9091	High Similarity	NPC9609
0.9091	High Similarity	NPC261004
0.9091	High Similarity	NPC191459
0.9091	High Similarity	NPC19687
0.9091	High Similarity	NPC143828
0.9091	High Similarity	NPC18607
0.9091	High Similarity	NPC22472
0.9091	High Similarity	NPC204854
0.9091	High Similarity	NPC115798
0.9091	High Similarity	NPC288669
0.9091	High Similarity	NPC152166
0.9091	High Similarity	NPC18772
0.9091	High Similarity	NPC7846
0.9085	High Similarity	NPC100916
0.9085	High Similarity	NPC265511
0.9085	High Similarity	NPC200388
0.9085	High Similarity	NPC55619
0.9079	High Similarity	NPC86485
0.9079	High Similarity	NPC476289
0.9079	High Similarity	NPC473664
0.9073	High Similarity	NPC252933
0.9073	High Similarity	NPC133953
0.9073	High Similarity	NPC50403
0.9073	High Similarity	NPC125062
0.9073	High Similarity	NPC200740
0.9073	High Similarity	NPC54394
0.9073	High Similarity	NPC28274
0.906	High Similarity	NPC12200
0.906	High Similarity	NPC62536
0.906	High Similarity	NPC33265
0.9057	High Similarity	NPC475434
0.9038	High Similarity	NPC414831
0.9032	High Similarity	NPC131557
0.9032	High Similarity	NPC471744
0.9028	High Similarity	NPC61546
0.9028	High Similarity	NPC72452
0.9026	High Similarity	NPC305663
0.9026	High Similarity	NPC110070
0.9026	High Similarity	NPC235215
0.9026	High Similarity	NPC189179
0.9026	High Similarity	NPC224137
0.9026	High Similarity	NPC163524
0.9026	High Similarity	NPC7973
0.9026	High Similarity	NPC176665
0.9026	High Similarity	NPC75215
0.9026	High Similarity	NPC108456
0.9026	High Similarity	NPC93376
0.9026	High Similarity	NPC472438
0.9026	High Similarity	NPC101830
0.9026	High Similarity	NPC78302
0.9026	High Similarity	NPC227192
0.9026	High Similarity	NPC203891
0.9026	High Similarity	NPC29841
0.9026	High Similarity	NPC287979
0.9013	High Similarity	NPC301123
0.9013	High Similarity	NPC55205
0.9007	High Similarity	NPC188871
0.9007	High Similarity	NPC149127
0.9007	High Similarity	NPC286342
0.9	High Similarity	NPC10304
0.9	High Similarity	NPC476342
0.9	High Similarity	NPC63256
0.8993	High Similarity	NPC153758
0.898	High Similarity	NPC124467
0.898	High Similarity	NPC185607
0.898	High Similarity	NPC214919
0.8974	High Similarity	NPC216092
0.8968	High Similarity	NPC193842
0.8966	High Similarity	NPC44573
0.8961	High Similarity	NPC98661
0.8961	High Similarity	NPC268161
0.8961	High Similarity	NPC49824
0.8961	High Similarity	NPC474520
0.8961	High Similarity	NPC245546
0.8961	High Similarity	NPC266960
0.8961	High Similarity	NPC43243
0.8961	High Similarity	NPC247017
0.8961	High Similarity	NPC292107
0.8954	High Similarity	NPC475895
0.8947	High Similarity	NPC208043
0.8947	High Similarity	NPC226973
0.8947	High Similarity	NPC308451
0.8947	High Similarity	NPC260895
0.894	High Similarity	NPC87125
0.894	High Similarity	NPC223579
0.894	High Similarity	NPC238366
0.894	High Similarity	NPC328119
0.894	High Similarity	NPC48479
0.894	High Similarity	NPC52005
0.894	High Similarity	NPC137062
0.894	High Similarity	NPC177298
0.894	High Similarity	NPC287101
0.894	High Similarity	NPC270465
0.894	High Similarity	NPC183950
0.8933	High Similarity	NPC470511
0.8926	High Similarity	NPC287275
0.8924	High Similarity	NPC475369
0.8917	High Similarity	NPC302741
0.8917	High Similarity	NPC475144
0.891	High Similarity	NPC269906
0.891	High Similarity	NPC243509
0.891	High Similarity	NPC130955
0.8903	High Similarity	NPC174908
0.8903	High Similarity	NPC471479
0.8903	High Similarity	NPC471515
0.8896	High Similarity	NPC80534
0.8896	High Similarity	NPC50715
0.8896	High Similarity	NPC201136
0.8896	High Similarity	NPC128863
0.8896	High Similarity	NPC201451
0.8896	High Similarity	NPC26227
0.8896	High Similarity	NPC214138
0.8896	High Similarity	NPC92659
0.8896	High Similarity	NPC227325
0.8896	High Similarity	NPC196439
0.8896	High Similarity	NPC44079
0.8896	High Similarity	NPC2476

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC474388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	987
0.2-0.3	1853
0.3-0.4	2643
0.4-0.5	1797
0.5-0.6	930
0.6-0.7	369
0.7-0.8	111
0.8-0.85	41
0.85-0.9	15
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9662	High Similarity	NPD3817	Phase 2
0.8859	High Similarity	NPD6799	Approved
0.8846	High Similarity	NPD919	Approved
0.8831	High Similarity	NPD2801	Approved
0.8742	High Similarity	NPD1512	Approved
0.8718	High Similarity	NPD3882	Suspended
0.8659	High Similarity	NPD4338	Clinical (unspecified phase)
0.8645	High Similarity	NPD6801	Discontinued
0.8645	High Similarity	NPD1934	Approved
0.8609	High Similarity	NPD1511	Approved
0.859	High Similarity	NPD7096	Clinical (unspecified phase)
0.8571	High Similarity	NPD6166	Phase 2
0.8571	High Similarity	NPD6168	Clinical (unspecified phase)
0.8571	High Similarity	NPD6167	Clinical (unspecified phase)
0.8553	High Similarity	NPD4378	Clinical (unspecified phase)
0.8545	High Similarity	NPD7808	Phase 3
0.8544	High Similarity	NPD7075	Discontinued
0.8537	High Similarity	NPD6797	Phase 2
0.8535	High Similarity	NPD5402	Approved
0.8516	High Similarity	NPD6599	Discontinued
0.8514	High Similarity	NPD2796	Approved
0.8485	Intermediate Similarity	NPD7251	Discontinued
0.8471	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD5403	Approved
0.8442	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD5494	Approved
0.8431	Intermediate Similarity	NPD5401	Approved
0.8415	Intermediate Similarity	NPD7054	Approved
0.8395	Intermediate Similarity	NPD3926	Phase 2
0.8385	Intermediate Similarity	NPD1247	Approved
0.8364	Intermediate Similarity	NPD7472	Approved
0.8354	Intermediate Similarity	NPD7819	Suspended
0.8354	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8293	Intermediate Similarity	NPD7473	Discontinued
0.8253	Intermediate Similarity	NPD7074	Phase 3
0.825	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1933	Approved
0.8113	Intermediate Similarity	NPD7411	Suspended
0.8105	Intermediate Similarity	NPD1243	Approved
0.8089	Intermediate Similarity	NPD920	Approved
0.8086	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD5844	Phase 1
0.8079	Intermediate Similarity	NPD3748	Approved
0.805	Intermediate Similarity	NPD4380	Phase 2
0.8039	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD6832	Phase 2
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD447	Suspended
0.7988	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1510	Phase 2
0.7952	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1549	Phase 2
0.7919	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3750	Approved
0.7815	Intermediate Similarity	NPD1240	Approved
0.7798	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7199	Phase 2
0.7712	Intermediate Similarity	NPD1607	Approved
0.7692	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2935	Discontinued
0.7677	Intermediate Similarity	NPD1551	Phase 2
0.7673	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3226	Approved
0.7651	Intermediate Similarity	NPD3749	Approved
0.7643	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5242	Approved
0.763	Intermediate Similarity	NPD6559	Discontinued
0.7619	Intermediate Similarity	NPD6959	Discontinued
0.759	Intermediate Similarity	NPD7768	Phase 2
0.7584	Intermediate Similarity	NPD3266	Approved
0.7584	Intermediate Similarity	NPD3267	Approved
0.7566	Intermediate Similarity	NPD2313	Discontinued
0.7561	Intermediate Similarity	NPD6386	Approved
0.7561	Intermediate Similarity	NPD6385	Approved
0.7547	Intermediate Similarity	NPD6190	Approved
0.7532	Intermediate Similarity	NPD230	Phase 1
0.753	Intermediate Similarity	NPD5353	Approved
0.7516	Intermediate Similarity	NPD2532	Approved
0.7516	Intermediate Similarity	NPD2533	Approved
0.7516	Intermediate Similarity	NPD2534	Approved
0.7516	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3146	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7485	Intermediate Similarity	NPD2403	Approved
0.7485	Intermediate Similarity	NPD1653	Approved
0.7484	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7468	Intermediate Similarity	NPD4307	Phase 2
0.7468	Intermediate Similarity	NPD943	Approved
0.7467	Intermediate Similarity	NPD1203	Approved
0.7451	Intermediate Similarity	NPD3268	Approved
0.7451	Intermediate Similarity	NPD6798	Discontinued
0.7451	Intermediate Similarity	NPD1296	Phase 2
0.7438	Intermediate Similarity	NPD3887	Approved
0.7417	Intermediate Similarity	NPD1019	Discontinued
0.7415	Intermediate Similarity	NPD17	Approved
0.741	Intermediate Similarity	NPD37	Approved
0.7405	Intermediate Similarity	NPD2346	Discontinued
0.7405	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2353	Approved
0.7403	Intermediate Similarity	NPD6233	Phase 2
0.7399	Intermediate Similarity	NPD3751	Discontinued
0.7383	Intermediate Similarity	NPD9717	Approved
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7377	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5953	Discontinued
0.7368	Intermediate Similarity	NPD3018	Phase 2
0.7362	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2797	Approved
0.7348	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5536	Phase 2
0.732	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD422	Phase 1
0.7312	Intermediate Similarity	NPD2800	Approved
0.7312	Intermediate Similarity	NPD2654	Approved
0.7308	Intermediate Similarity	NPD6355	Discontinued
0.7303	Intermediate Similarity	NPD2798	Approved
0.7294	Intermediate Similarity	NPD6234	Discontinued
0.7285	Intermediate Similarity	NPD3225	Approved
0.7278	Intermediate Similarity	NPD7033	Discontinued
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2981	Phase 2
0.7267	Intermediate Similarity	NPD1608	Approved
0.7263	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7286	Phase 2
0.7255	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD411	Approved
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7222	Intermediate Similarity	NPD2354	Approved
0.7219	Intermediate Similarity	NPD2983	Phase 2
0.7219	Intermediate Similarity	NPD2982	Phase 2
0.7208	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1652	Phase 2
0.7188	Intermediate Similarity	NPD1471	Phase 3
0.7166	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7095	Approved
0.7161	Intermediate Similarity	NPD3027	Phase 3
0.716	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6651	Approved
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7125	Intermediate Similarity	NPD6099	Approved
0.7125	Intermediate Similarity	NPD6100	Approved
0.7118	Intermediate Similarity	NPD4288	Approved
0.711	Intermediate Similarity	NPD8127	Discontinued
0.7095	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4340	Discontinued
0.7081	Intermediate Similarity	NPD2344	Approved
0.707	Intermediate Similarity	NPD4062	Phase 3
0.7069	Intermediate Similarity	NPD7229	Phase 3
0.7048	Intermediate Similarity	NPD5049	Phase 3
0.7041	Intermediate Similarity	NPD5890	Approved
0.7041	Intermediate Similarity	NPD5889	Approved
0.7039	Intermediate Similarity	NPD7038	Approved
0.7039	Intermediate Similarity	NPD7039	Approved
0.7039	Intermediate Similarity	NPD3972	Approved
0.7035	Intermediate Similarity	NPD6971	Discontinued
0.703	Intermediate Similarity	NPD7390	Discontinued
0.7025	Intermediate Similarity	NPD4060	Phase 1
0.7006	Intermediate Similarity	NPD7228	Approved
0.7006	Intermediate Similarity	NPD2163	Approved
0.7	Intermediate Similarity	NPD9268	Approved
0.7	Intermediate Similarity	NPD5005	Approved
0.7	Intermediate Similarity	NPD7549	Discontinued
0.7	Intermediate Similarity	NPD5006	Approved
0.6993	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5535	Approved
0.6982	Remote Similarity	NPD6585	Discontinued
0.6982	Remote Similarity	NPD4972	Discontinued
0.6981	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5124	Phase 1
0.6977	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5710	Approved
0.6971	Remote Similarity	NPD5711	Approved
0.6963	Remote Similarity	NPD7435	Discontinued
0.6961	Remote Similarity	NPD8312	Approved
0.6961	Remote Similarity	NPD8313	Approved
0.6957	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4110	Phase 3
0.6951	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.694	Remote Similarity	NPD8150	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data